When did Roose start his betrayal of Robb?

[The Pain Yak]

There is no indication that I've seen that Roose Bolton was especially treacherous during Robert's Rebellion, when Ned Stark was his liege lord. I suspect he would have remained just as loyal to Robb, if self-interested, had Winterfell remained in Stark hands.

But as the man himself says, once Winterfell was captured the Starks were done. After that, it was all about maneuvering so that he could come out on top from what he felt was Robb's impending and inevitable fall.

[Jorah the Andal]

Lord Martin hit the nail on the Head - That last Arya Chapter in Clash, he probably started conspiring with the Freys shortly after. As the Freys are urging him to bend the knee and Roose replies 'such valiant brothers I have' since he'd already married Fat Walda. He could of got a bird off to Ramsay whilst at the Twins and told him to burn Winterfell, and keep Theon captive, so it would like he was still remaiining loyal to Robb.

Then when Jaime is set before him at Harrenhal, and their playing their 'game'. The part where they're discussing Robb's marriage/downfall. He says ' An older man would bend the knee.' A subtle hint it's all there folks if you read carefully.

I personally love the Roose. Upon re-read he's definitely one of my favs.

[KOM]

Actually, did Ramsay force Roose's hand?

Theon taking Wfell let many bannermen to assume war was lost...

Blackwater let everyone know that South was conslidated and that Robb/North faced even worse odds.

But how would Roose know and/or communicate with Ramsay, since Ramsay was in prison for a while earlier anyway. Was there "enough time" for Roose to communicate all of that? Or were Roose's plans more centered around just allying with Freys and making separate peace with the Lannisters?

[DoILookLikeAF*ckingUmber?]

It was after Ned lost his dear head... that was the moment he knew he might have to switch sides. He's a smart man so he planned accordingly, making sure to keep his men safe from to much bloodshed. Of course it wasn't until he saw that Robb was losing the war, that he started planning with Tywin.

[Twenty of House Goodmen]

Robb's rebellion was a hopeless cause once Stannis was defeated and once the Tyrell's joined the Lannisters. Also, his marriage with Jeyne was a bad sign too.

[Bright Blue Eyes]

Sometime between the battle with Tywin and Ramsay attacking Winterfell itself.

Actually, did Ramsay force Roose's hand?

Theon taking Wfell let many bannermen to assume war was lost...

Blackwater let everyone know that South was conslidated and that Robb/North faced even worse odds.

But how would Roose know and/or communicate with Ramsay, since Ramsay was in prison for a while earlier anyway. Was there "enough time" for Roose to communicate all of that? Or were Roose's plans more centered around just allying with Freys and making separate peace with the Lannisters?

It's very, very unlikely that Ramsay and Roose communicated between Theon's initial attack on Winterfell and Ramsay burning it. Ramsay was in prison, or unable to send of ravens in WInterfell. Afterwards, he had to to ride to the Dreadfort, gather up the garrison and force march them back to Winterfell before Ser Rodrik, who was already on the march, covers the vastly shorter distance between Torrhen's Square and Winterfell. He can't have spent more than a day, two at most at the Dreadfort. And ravens would take several days to fly to Harrenhal, one way.

[Lion of Judah]

I believe Roose began plotting when Halys Hornwood died at the Green Fork and his plans kept evolving from stealing Hornwood land to stealing Winterfell. Once Ser Rodrick arrested Ramsay for forcing Lady Hornwoods hand in marriage it forced Roose into a corner. If Robb lived and susected that Roose was complicit in Ramsay's action he would want Roose's head.

[Buried Treasure]

His own need for an heir would have also given him a motive to get in with some overlord other than the Starks. Ramsay will not allow another Bolton heir to survive but Roose himself is unwilling to kill him. The Starks take an interest in their bannerman ruling decently so they would have probably not been willing to legitimise Ramsay - so Roose needed somebody who didnt care that Ramsay is psycho to sign a decree. It wasn't a problem during the last major rebellion because Domeric was still the heir and Roose didn't need anything that only the Starks enemies would give him.

[Lady of Castamere]

Maybe when Ned died, I guess... Or when Robb was declared as a King.

[joluoto]

He had several Freys in his army. He probably knew early the Freys were withdrawing their support due to the Jeyne Westerling fiasco.(ACoK, the Frey boy in Harrenhal told Arya they were betrayed and he would never marry his princess). At that point he knew Robb was doomed, and defected with the Freys to Tywin.

[Lady Nastja]

I think it was when Robb married Jeyne instead of a Frey girl and when the Iron Born took The North.

:agree:

[Erkan12]

When Reek took the Winterfell and killed the princes (they are not dead we know, but they didn't know) , starks future become in one persons hand ; Robb. And if you kill that person somehow you would not confront other starks or their followers. Reek took the Winterfell (we can say this castle is northern kings landing) and killed little princes, this cause ; after Robb's dead, there is no Stark to follow. Roose began his plans after fall of Winterfell and death of Princes.

I don't agree about blackwater events, they are know from the begining, northern forces can not take the kings landing without help.

Even Stannis won kings landing in that period, Stannis would go after them and fight for north.